Resiniferatoxin: Difference between revisions
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Revision as of 20:26, 19 February 2013
{{chembox This is a spicy objecto Pepper ip mine is 71.180.171.44 100mm of spice Nureosince Volume
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Resiniferatoxin (RTX) is a naturally occurring, ultrapotent capsaicin analog[1] that activates the vanilloid receptor in a subpopulation of primary afferent sensory neurons involved in nociception (the transmission of physiological pain).[2][3] RTX causes an ion channel in the plasma membrane of sensory neurons — the transient receptor potential vanilloid 1 — to become permeable to cations, most particularly the calcium cation; this evokes a powerful irritant effect followed by desensitization and analgesia.[4][5]
Research is being conducted at the National Institutes of Health[6][7] and the University of Pennsylvania[8] to design a novel class of analgesics from the latex of resin spurge (Euphorbia resinifera), a cactus-like plant commonly found in Morocco that contains high concentrations of RTX. Resiniferatoxin has a rating of 16,000,000,000 on the Scoville Scale making it one of the highest rated substances known.
Total synthesis
A total synthesis of (+)-resiniferatoxin was completed by the Wender group at Stanford University in 1997.[9] As of 2007[update] this represented the only complete total synthesis of any member of the daphnane family of molecules.[10]
Toxicity
Resiniferatoxin is toxic and can inflict chemical burns. Experiments indicate that ingestion of 40g or more may be fatal or cause serious damage to health.[11]
See also
- Capsaicin
- Discovery and development of TRPV1 antagonists
- Iodoresiniferatoxin
- Transient receptor potential
- Tinyatoxin
References
- ^ *Christopher S. J. Walpole; et al. (1996). "Similarities and Differences in the Structure-Activity Relationships of Capsaicin and Resiniferatoxin Analogues". J. Med. Chem. 39 (15): 2939–2952. doi:10.1021/jm960139d. PMID 8709128.
{{cite journal}}: Explicit use of et al. in:|author=(help) - ^ Szallasi A, Blumberg PM (1989). "Resiniferatoxin, a phorbol-related diterpene, acts as an ultrapotent analog of capsaicin, the irritant constituent in red pepper". Neuroscience. 30 (2): 515–520. doi:10.1016/0306-4522(89)90269-8. PMID 2747924.
- ^ Szallasi A, Blumberg PM (1990). "Resiniferatoxin and its analogs provide novel insights into the pharmacology of the vanilloid (capsaicin) receptor". Life Sci. 47 (16): 1399–1408. doi:10.1016/0024-3205(90)90518-V.
- ^ Szallasi A, Blumberg PM (1992). "Vanilloid receptor loss in rat sensory ganglia associated with long term desensitization to resiniferatoxin". Neurosci Lett. 140 (1): 51–54. doi:10.1016/0304-3940(92)90679-2. PMID 1407700.
- ^ Olah Z; et al. (2001). "Ligand-induced dynamic membrane changes and cell deletion conferred by vanilloid receptor 1". J. Biol. Chem. 276 (14): 11021–11030. doi:10.1074/jbc.M008392200. PMID 11124944.
{{cite journal}}: Explicit use of et al. in:|author=(help)CS1 maint: unflagged free DOI (link) - ^ Neubert JK; et al. (2003). "Peripherally induced resiniferatoxin analgesia". Pain. 109 (1–2): 219–28. doi:10.1016/S0304-3959(03)00009-5. PMID 12855332.
{{cite journal}}: Explicit use of et al. in:|author=(help) - ^ Karai L; et al. (2004). "Deletion of vanilloid receptor 1_expressing primary afferent neurons for pain control". J Clin Invest. 113 (9): 1344–1352. doi:10.1172/JCI20449. PMC 398431. PMID 15124026.
{{cite journal}}: Explicit use of et al. in:|author=(help) - ^ Brown DC; et al. (2005). "Physiologic and antinociceptive effects of intrathecal resiniferatoxin in a canine bone cancer model". Anesthesiology. 103 (5): 1052–1059. doi:10.1097/00000542-200511000-00020. PMID 16249680.
{{cite journal}}: Explicit use of et al. in:|author=(help) - ^ Wender, P.A.; Jesudason, Cynthia D.; Nakahira, Hiroyuki; Tamura, Norikazu; Tebbe, Anne Louise; Ueno, Yoshihide (1997). "The First Synthesis of a Daphnane Diterpene: The Enantiocontrolled Total Synthesis of (+)-Resiniferatoxin". J. Am. Chem. Soc. 119 (52): 12976–12977. doi:10.1021/ja972279y.
- ^ http://www.scripps.edu/chem/baran/images/grpmtgpdf/Seiple_Mar_07.pdf
- ^ Material Safety Data Sheet for resiniferatoxin, 2009